I would be very careful about this approach with “rent-to-own.” If you tack on a lot of fees and threaten to (or end up) rescind the contract due to failure-to-maintain, this looks a lot like predatory lending. Anything involving judgment is going to be a hassle and maybe get you into trouble. (“You have to fix this scratch in the countertop – no I don’t. You put a burn mark in the sink you have to repair that – no I don’t”). By the time you’re done, you’ll be in the same place you would have been (with the tenant leaving in a huff and you get the home back in whatever condition).
It also looks a lot like regular renting but with inspections & maintenance hassle which is the same as regular renting with more pickiness in “ongoing” inspections with the threat of fines & we-ll have-it-done-whether-you-like-it-or-not.
If you want to do it with “regular renting” you’ll find out what your local judge allows once it comes up in court (i.e., during eviction for non-payment). Otherwise you can do and say what you want and if they pay then they pay and if they don’t then you evict. And same goes for rent-to-own.
You can be as picky as you want as long as you have the demand. Of course, it is best to be picky up front if you have the demand. Once you’ve “closed the deal” so to speak you have to “train them” to do things “your way” somehow. If they don’t get with your program, you start over with the next in line.
The thing you have to look out for is being accused of using the “failure to maintain” part of a contract to pressure the homeowner (or resident with “equity” in the home) to bow to your “unfair” demands or be sued for breach of contract.
Renting to someone while you SEE if they are a good candidate for homeowner is not the same thing. “Rent from us for a year and then we’ll see” is not the same as “Rent from us for 5 years and then the home is yours” but then you kick them out in month 6 or 16.